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Chester VT Real Estate

Located in Windsor County, Chester is a wonderful New England town reminiscent of a bygone era. With architecture pre-dating the civil war, Chester is rich in history and beauty. Although historic, the quaint town is thriving with its unique markets, galleries, and restaurants that offer much to do. The town is also conveniently located close to Okemo Mountain and Mount Snow for those who enjoy outdoor recreation as well as within driving distance to Manchester, VT

Search the latest real estate in Chester, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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134 Gold River Extension Chester VT 05143

Chester, VT134 Gold River Extension

Price$1,490,000The price has recently decreased

Active With Contract

MLS Number 4837125

  • Commercial
  • Acreage 13.42

Rare opportunity with commercial/industrial zoning. 13+ acres of fully permitted subdividable lots. Property can be used in its entirety, or use what you need and market the permitted land parcels to others. Currently there are 6 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, and rail siding; 7544 sq ft open span, no ceilings, storage building; 3 additional storage buildings. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Large former ore shed with 7544 sq ft of open span. Multiple doors to access the building. Survey and permits in place for 7 lot subdivision of the industrial park. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Also offered separately (building lot, ore shed building, or garage/office/storage buildings). Video attached to the MLS.

Listed by Andy Paluch of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$925,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Area Near Skiing, Rural
  • Acreage 526.4
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 526 +/- acres has it all. Made up of 4 contiguous preexisting lots the parcel has road frontage on Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see today!!

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

816 Popple Dungeon Road Chester VT 05143

Chester, VT816 Popple Dungeon Road

Price$850,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4848206

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,676

Welcome to Deer Valley Farm also known as the Williams Homestead. This is the first time the property has been offered for sale in over 60 years! The home has been lovingly cared for with lots of improvements over the decades of ownership. Outside: The barn has undergone major work which insures its stability for years to come and includes a wine cellar. It measures 45x105 with plenty of room for cars, toys or animals. Other improvements include stonework, tennis court and pool with pool house and gardens. The walking bridge over the Williams River includes 4 staircases to the river and built in lights. The home is styled with Italian tile throughout and offers cozy antique charm with 3 fireplaces. The home does need updating but will be well worth the effort. The structure itself has been well maintained. The large acreage easily lends itself to a few other incredible homesites. Located just outside the town of Chester less than 4 hours to NYC and 2.5 hours to Boston. Minutes to all of Southern Vermont amenities including Okemo, Stratton, Killington, Vermont Country Store, Weston Playhouse, world-class golf and the shops in Manchester. This property will not disappoint.

Listed by Lisa Kelley of Cummings & Co

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

698 Vermont RT 11 Chester VT 05143

Chester, VT698 Vermont RT 11

Price$650,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4820671

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 12
  • Square Feet 6,848

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

698 VT ROUTE 11 West Chester VT 05143

Chester, VT698 VT ROUTE 11 West

Price$650,000The price has recently decreased

MLS Number 4820670

  • Commercial
  • Year Built 1810
  • Acreage 5.63

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$529,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4845016

  • Residential Single Family
  • Bathroom 9
  • Bedrooms 9
  • Construction Existing
  • Square Feet 5,242

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches. The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$529,000The price has recently decreased

MLS Number 4837044

  • Commercial
  • Year Built 1780
  • Acreage 0.75

This circa 1780's stunning, country inn is located in the heart of Chester and southern Vermont, the ideal setting for a hospitality business. Owned and operated with care, this home and it's owners have provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. This well established business is ready for you to put your mark on the hospitality for the long list of returning guests! The 7 guest rooms and common areas are fully furnished. The newly renovated owners quarters, including two spacious bedrooms, will be unfurnished allowing your own personal décor. Enjoy a comfortable lifestyle in Vermont, in concert with your guests! The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax. The central village location allows easy access to the surrounding community on foot!. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney and Joan Morey of Barrett & Valley Associates,Inc/Chest

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

690 Trebo Road Chester VT 05143

Chester, VT690 Trebo Road

Price$475,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 4877533

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,112

Country colonial playground - Everything just feels right from the moment you pull in the driveway and slide into the large two car attached garage. Spacious oversized modern kitchen with cozy woodstove in the dining area will keep you warm on those long winter days. A half bath, bedroom and "comfy" living room round out the main floor. A large deck spans the full width of the house to take in the beautiful eastern views and fields. Upstairs are a private master suite with a beautiful tiled bath, two bedrooms and another tiled bath. The full basement is ready for a transformation to a movie or rec room. Current owners have sheep and chickens but you can remove the fencing and open the land back up. There are endless trails woven throughout the 19 acres consisting of open fields and woodland. There's even a small creek that runs through the bottom corner of the lot. Outbuildings consist of a heated "she shed", a free standing two car work barn, a run in shed and a chicken coop. This updated home is equipped with a state of the art solar array. If you are looking for your slice of Vermont, this charming house is minutes off Rte 103 and a five minute ride to Smitty's general store for some of the best deli meats, craft beer and sandwiches in the area.

Listed by Katherine Burns of William Raveis Vermont Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

134 Gold River Extension Chester VT 05143

Chester, VT134 Gold River Extension

Price$460,000The price has recently decreased

Active With Contract

MLS Number 4837151

  • Commercial
  • Acreage 2.49

Rare opportunity with commercial/industrial zoning. 2.49 acres that is fully permitted. Property can be used as one business spot, or share the office building with another business. Currently there are 3 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, office, and rail siding; plus an additional 1500 sq ft storage building. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Also available separately (building lots, ore shed building, or the entire parcel-see MLS 4837125). Video attached to the MLS.

Listed by Andy Paluch of TPW Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

292 Quarry Road Chester VT 05143

Chester, VT292 Quarry Road

Price$449,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4878315

  • Residential Single Family
  • Square Feet 1,880
  • Bedrooms 3
  • Construction Existing
  • Bathroom 4

Overlooking the south branch of the Williams River, this expansive, 3+ bedroom, 3.5 bath 2006 contemporary home on 5 acres +/- is located on a country road just outside the village of Chester. With a subtle nod to Victorian style and high ceilings throughout, there are many attractive features to enjoy such as an open kitchen/living area with breakfast bar, wood stove and half-bath located near the mudroom entry. Lovely interior French doors open to the living room with a formal gas fireplace and bay window alcove, an inviting foyer, a first floor study/office, and a wonderful sunroom with floor to ceiling windows flanked by two deck/patios. The second floor features a large, private en suite bedroom with a large walk-in closet and full bath. The relaxing sounds of the river can be heard from the two additional bedrooms connected by a full bath and laundry. The walkout basement has a large, semi-finished space that would make a terrific game room or in-law apt with a 3/4 bath, a work sink, laundry hook-ups in place and a storage room accessed on either side of the basement. The attached two car garage adjoins the mudroom entry includes workshop space, and a large, second floor unfinished bonus space that could serve as a home office. The landscaped grounds feature two decks, a covered porch, perennial gardens and a riverside firepit accented by a dramatic vertical stone. A path through the woods leads to a super cool treehouse with a swing for two!

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

32 VT Rte 10 Chester VT 05143

Chester, VT32 VT Rte 10

Price$449,000The price has recently decreased

MLS Number 4880525

  • Commercial
  • Year Built 1980
  • Acreage 9.4

Incredible commercial location in Chester, VT! Property is on 10 acres with mountain views & mature fruit trees, near Okemo ski area & historic Chester Village. This property sits at a major intersection - VT Rte 103 and VT Rte 10 connecting Springfield and Ludlow on the main east/west route to Rutland. Formerly a retail establishment selling local farm products, prepared foods, local art, and featuring a wide array of local artisan's goods. Commercial kitchen fully outfitted, includes Vulcan range/oven, griddle, grill, Hobart meat slicer, mixer, deep fryer, auto dishwasher, ice machine and huge walk-in freezer & refrigerator & more. Permitting supports restaurant seating of 22. Currently vacant on the main level with a solid long term renter in the 3 BR apartment on the upper level. Great income producing rental unit. Accessory building has a foundation and 6' knee walls in place for hoop barn or the like. Formerly used as livestock barn with storage area framed & water/power installed. Easy to re-purpose for your use. Additional shed building formerly used to smoke & cure meats available for your use too. Bring your ideas and plans. This property has strong potential for gas/convenient mart, drive-in theater or the like. Great daily traffic with hundreds of cars passing daily...year round! Locals and visiting traffic all use this thoroughfare for steady traffic flow. Don't miss this opportunity to capitalize on this great location. Schedule a showing today!

Listed by Kevin Channell of Bassette Real Estate Group

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

372 Main Street Chester VT 05143

Chester, VT372 Main Street

Price$439,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4880263

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,775

This exquisite home has been tastefully renovated throughout. The front porch invites a bit of respite and observation with a pause now and then as folks walk by with a hello. A visit offers quite a surprise in terms of the spacious floor plan and great flow! Family and friends easily gather throughout the common space, yet plenty of quiet time area is available. The modern kitchen is open, with ample stone counter tops, and newer appliances. The pantry has been saved and serves as incredible storage! A large office or den is adjacent to an expansive great room combination. A full bath is located just off the kitchen. The second floor landing is comfortable introducing four bedrooms and a full bath and a laundry. The great carriage barn retains it's one holer and has had substantial work done to add to it's long life. It is an incredible building to explore! The side yard is level and enjoys a patio offering expanded fair weather family enjoyment.

Listed by Amanda Stearns and Joan Morey of Barrett & Valley Associates,Inc/Chest

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.09% last updated on 2021-10-21

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 26, 2021.

 

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